Is there a limit on how many Direct Rollovers I can do in one year?

You're actually in good shape! The "once per year" rule only applies to IRA-to-IRA rollovers where you personally receive the funds (indirect rollovers). Direct rollovers from employer plans (401k, 457b) to IRAs have no annual limit - you can do as many as you want in a year. Let me break it down: - Transaction #1: 401k to Traditional IRA (unlimited) + Traditional to Roth conversion (unlimited) - Transaction #2: 401k to Roth IRA (unlimited) - Transaction #3: 457 Plan to Traditional IRA (unlimited) The key is that you're moving from employer plans TO IRAs, not between IRAs. Also, Roth conversions (where you pay taxes to convert Traditional IRA money to Roth) have no annual limits. The only concern would be properly calculating and paying taxes on the pre-tax to Roth conversions, but it sounds like you've already handled that by pre-paying taxes.

I had a similar situation last year and discovered taxr.ai (https://taxr.ai) after getting confused by conflicting advice online. What helped me was their document analysis tool that reviewed my 1099-R forms and immediately identified which transactions were taxable conversions vs. non-taxable rollovers. Their system explained exactly which parts of my rollovers would trigger taxes and which wouldn't. In my case, they found that my plan administrator had incorrectly coded one of my distributions which would have caused major headaches with the IRS if I hadn't caught it. The website lets you upload all your tax docs and then explains everything in plain English instead of tax jargon. Super helpful for complex rollover situations like yours.

I wanted to follow up on my skeptical comment. I tried taxr.ai and I'm honestly impressed. I uploaded my 1099-R forms and my old tax returns, and it immediately identified a pro-rata issue with my backdoor Roth contribution that my CPA missed last year! It showed me exactly how to calculate the taxable portion using Form 8606 and explained why my previous approach was wrong. The system caught that I had been incorrectly treating my rollovers as entirely tax-free when a portion should have been taxed due to having other IRA balances. It also confirmed that there's no limit on direct rollovers from employer plans to IRAs, which is exactly what the original poster was asking about. Saved me a ton of confusion and potentially an audit.

If you're still confused or worried about your rollover situation, you might want to call the IRS directly to get confirmation. I was in rollover hell last year and spent HOURS trying to get through to an IRS agent who could help. After 9 attempts and waiting on hold for a combined 7+ hours, I found Claimyr (https://claimyr.com) and watched their demo (https://youtu.be/_kiP6q8DX5c). Their service basically waits on hold with the IRS for you and calls you when an actual human agent is on the line. I was super skeptical, but I was desperate after weeks of trying. They got me connected to a retirement specialist at the IRS within 2 hours who answered all my rollover questions and even documented our conversation in my file in case of future questions. Saved me tons of stress, especially since online advice can be contradictory when dealing with multiple rollovers like your situation.

I have to eat crow and admit I was wrong about Claimyr. After my skeptical reply, I decided to try it since I needed to talk to someone about my own rollover issue that I couldn't figure out. I had done multiple rollovers including a 403b to Roth conversion and couldn't figure out how to properly report it. The service actually worked - they called me back in about 90 minutes with an IRS agent on the line. The agent confirmed that there's no limit on direct rollovers from employer plans, clarified exactly how to report my 403b to Roth conversion on Form 8606, and even helped me understand the tax withholding requirements for future conversions. Definitely worth it for complex tax situations like multiple rollovers where the online advice conflicts. Sometimes you just need to hear it directly from the IRS.

I think there's some confusion in this thread about the once-per-year rule. It specifically applies to IRA-to-IRA rollovers where you take possession of the funds (receive a check). The rule states you can only do ONE IRA-to-IRA indirect rollover in a 12-month period (not calendar year). This limit applies across all your IRAs combined - traditional, Roth, SEP, and SIMPLE IRAs are all counted together. But important exceptions that DO NOT count toward this limit: - Rollovers from employer plans (401k, 403b, 457) to IRAs (unlimited) - Roth conversions (traditional IRA to Roth IRA) (unlimited) - Trustee-to-trustee transfers between IRAs (unlimited) So in the OP's case, none of those transactions are limited since they're coming from employer plans.

Important note: while there's no limit on how many direct rollovers you can do from employer plans to IRAs, make sure you're tracking the tax implications correctly! When moving pre-tax money (like from a traditional 401k) directly to a Roth IRA, that's a conversion that's fully taxable in the year you do it. It sounds like you've already planned for this by pre-paying taxes, but make sure you're tracking the exact amounts from each rollover. Also, if you're doing multiple rollovers, keep very detailed records of each transaction - dates, amounts, account numbers, etc. The IRS can get suspicious with multiple retirement account movements in one year, not because it's not allowed, but because it's easy to make reporting errors.

Great question! I went through a similar situation last year with multiple rollovers and was equally confused about the rules. The good news is that you're completely fine - there's no annual limit on direct rollovers from employer plans to IRAs. The "once per year" rule that causes so much confusion only applies to indirect IRA-to-IRA rollovers where you personally receive the funds (like getting a check made out to you). Since all your transactions were from employer plans (401k, 457) to IRAs, they're unlimited. One thing to double-check: make sure your tax prepayment of $17,000 covers the full tax liability from your pre-tax to Roth conversions. You'll want to calculate the exact taxable amounts from each conversion to ensure you're not underpaid. The IRS can be pretty strict about estimated tax payments when you have large conversion amounts. Also, keep detailed records of all your 1099-R forms and any correspondence from your plan administrators. With multiple rollovers in one year, good documentation will save you headaches if the IRS has questions later.

Just wanted to add some perspective as someone who works in retirement plan administration. The confusion around rollover limits is incredibly common, and you're definitely not alone in worrying about this! To reinforce what others have said: your transactions are all perfectly fine. The annual limit only applies to IRA-to-IRA indirect rollovers (where you receive a check), not employer plan rollovers. We process hundreds of these types of rollovers every year without any issues. One thing I'd recommend is requesting written confirmation from each of your plan administrators that the transactions were processed as direct rollovers. This gives you additional documentation beyond just the 1099-R forms. Most administrators will provide a simple letter confirming the rollover details if you request it. Also, regarding your tax prepayment strategy - that was really smart planning! Many people get caught off guard by the tax liability from large conversions. Just make sure to save copies of your estimated tax payment confirmations, as you'll need to reference these when filing your return to show the IRS that taxes were already paid on the conversion amounts. The IRS actually likes to see this kind of proactive tax planning, so you're in good shape both from a compliance and a planning perspective.

I'm a newcomer here but went through a very similar situation last year with multiple employer plan rollovers, so I thought I'd share what I learned! First off, you're absolutely fine - no limits on direct rollovers from employer plans to IRAs. I did four separate rollovers in one tax year (two 401k rollovers, one 403b, and one 457 plan) and had zero issues with the IRS. The key thing that helped me was creating a simple tracking spreadsheet right away with columns for: transaction date, source plan type, amount rolled over, destination account, and whether it was taxable (like your pre-tax to Roth conversions). This made tax filing so much easier. One thing I wish someone had told me earlier: if you're doing multiple conversions like you did, consider making additional estimated tax payments throughout the year rather than just the one large prepayment. The IRS prefers to see payments spread out quarterly, and it can help avoid any underpayment penalties if your conversion amounts end up being larger than expected. Also, when your 1099-R forms arrive, double-check that each one shows the correct distribution code for rollovers (usually "G" for direct rollovers). I had one plan administrator incorrectly code a rollover as a regular distribution, which would have caused major tax headaches if I hadn't caught it. You sound like you planned this really well with the tax prepayment strategy. Most people don't think ahead like that!

As someone new to this community, I want to thank everyone for the incredibly detailed and helpful responses! This thread has been a goldmine of information about rollover rules and tax implications. I'm in a somewhat similar situation - planning to do multiple rollovers next year from different employer plans, and I was really worried about potential limits or complications. Reading through all these experiences and expert advice has given me so much clarity on what's allowed and what to watch out for. A few key takeaways I'm noting for my own planning: - No limits on direct rollovers from employer plans to IRAs (huge relief!) - The once-per-year rule only applies to indirect IRA-to-IRA rollovers - Proper documentation and record-keeping is absolutely critical - Quarterly estimated tax payments might be better than one lump sum - Double-check those 1099-R distribution codes when they arrive @KingKongZilla - it sounds like you had great foresight with your tax prepayment strategy. That kind of planning ahead really shows you understood the tax implications of your conversions. Does anyone have recommendations for good tax software that handles complex rollover situations well? I want to make sure I'm prepared for proper reporting when the time comes.

Welcome to the community! I'm new here as well and have been following this discussion with great interest since I'm planning some similar rollover moves myself. @KingKongZilla - your situation is actually a great example of smart retirement planning! The fact that you prepaid taxes shows you really understood the implications of your conversions. Based on all the expert responses here, it's clear you're completely in compliance with IRS rules. I wanted to add one additional resource that might be helpful for anyone dealing with complex rollover situations: the IRS Publication 590-A and 590-B. These publications specifically cover IRA contributions, distributions, and rollovers. While they can be dense reading, they're the official source for all the rules everyone has been discussing here. Also, for those planning future rollovers, I've learned from this thread that timing can be important. If you're doing multiple conversions that will push you into higher tax brackets, you might want to spread them across multiple tax years rather than doing everything at once like the OP did (though his prepayment strategy was brilliant). Has anyone here had experience with splitting large conversions across multiple years to manage the tax impact? I'm wondering if that's a strategy worth considering for my own situation. Thanks to everyone who has shared their knowledge and experiences - this community is incredibly helpful for navigating these complex tax situations!

Welcome to the community! As a newcomer, I found this thread incredibly helpful since I'm also planning some retirement account moves next year and was confused about the rollover rules. From reading all the detailed responses here, it's clear that @KingKongZilla's situation is completely compliant with IRS regulations. The distinction between employer plan rollovers (unlimited) and IRA-to-IRA rollovers (limited to once per year for indirect rollovers) is really important and not well explained in most online resources. I particularly appreciated the advice about documentation and record-keeping. As someone who tends to be disorganized with financial paperwork, the suggestion to create a tracking spreadsheet with transaction dates, amounts, and account details seems like it could save major headaches during tax season. One question for the community: for those who have done multiple rollovers like this, do you recommend working with a tax professional for the first year, or are the major tax software packages sufficient for handling the Form 8606 reporting requirements? I'm trying to decide between DIY and professional help for my own upcoming rollover situation. Thanks to everyone who shared their experiences and expertise - this community seems like a great resource for navigating complex tax situations!

Welcome to the community! As a newcomer, I've been following this thread with great interest since I'm planning some retirement account consolidation moves myself and was initially worried about potential IRS limits. It's incredibly reassuring to see such detailed and knowledgeable responses confirming that @KingKongZilla's multiple rollover strategy is completely compliant. The distinction between unlimited employer plan rollovers versus the once-per-year limit on indirect IRA-to-IRA rollovers is something I definitely didn't understand before reading this discussion. I'm particularly impressed by the proactive tax planning approach of prepaying $17,000 to cover the conversion taxes. That level of forward thinking really shows a solid understanding of the tax implications involved in pre-tax to Roth conversions. For others like me who are planning similar moves, I'm taking note of several key strategies mentioned here: creating detailed transaction tracking spreadsheets, requesting written confirmation letters from plan administrators, and carefully reviewing 1099-R distribution codes when they arrive. The emphasis on documentation throughout this thread really highlights how important proper record-keeping is for complex rollover situations. One question for the community: has anyone had experience with the IRS requesting additional documentation or clarification for multiple rollover transactions in a single year, even when everything was done correctly? I'm curious if having several rollovers might trigger any additional scrutiny during processing, or if it's typically routine as long as the paperwork is properly filed. Thanks to everyone who has shared their expertise - this has been an incredibly educational discussion!

Welcome to the community! As a newcomer here, I've been following this discussion closely since I'm dealing with some retirement account moves myself and was initially concerned about IRS rollover limits. It's really encouraging to see such thorough and expert responses confirming that your multiple rollover strategy is completely legitimate. The key distinction everyone has highlighted - that employer plan rollovers are unlimited while only indirect IRA-to-IRA rollovers have the once-per-year restriction - is something I definitely didn't grasp before reading this thread. Your proactive approach of prepaying $17,000 in taxes for the conversions shows excellent planning. That kind of forward thinking on the tax implications really demonstrates you understood what you were getting into with those pre-tax to Roth moves. One thing I'm taking away from all the advice here is the critical importance of documentation. The suggestions about creating transaction tracking spreadsheets, requesting written confirmations from plan administrators, and carefully reviewing those 1099-R forms when they arrive all seem like essential steps for anyone doing multiple rollovers. Based on everything I've read in this thread, you handled your situation really well and should have no issues with the IRS. The combination of proper planning, tax prepayment, and what sounds like good record-keeping puts you in an excellent position come tax filing time. Thanks for asking this question - your situation and all the expert responses have been incredibly educational for those of us planning similar retirement account strategies!